Email this article Functionalization of 4-hydroxy-6-methyl-2Н-pyran-2-one under the conditions of the modified Biginelli reaction
- Authors: Kanevskaya I.V1, Pchelintseva N.V1, Fedotova O.V1
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Affiliations:
- Saratov State University
- Issue: Vol 59, No 4 (2023)
- Pages: 466-474
- Section: Articles
- URL: https://journals.rcsi.science/0514-7492/article/view/144750
- DOI: https://doi.org/10.31857/S0514749223040055
- EDN: https://elibrary.ru/ARIOMH
- ID: 144750
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Abstract
The features of the interaction of 4-hydroxy-6-methyl-2 H -pyran-2-one with aromatic aldehydes and urea in the one-pot mode of the classical mode, as well as using thermal and microwave activation of The Biginelli reaction variants, were studied. Depending on the conditions of single-reactory processes, previously unknown 3-[amino(aryl)methyl]-4-hydroxy-6-methyl-2 H -pyran-2-one, arylmethylenebis-4-hydroxy-6-methyl-2 H -pyran2-one, hybrid system - 2-hydroxy-7-methyl-4-(3-nitrophenyl)-4,4a-dihydro-5 H -pyrano[4,3- d ]pyrimidine-5-one in the case of transformation with aryl aldehyde containing an electron-acceptor substitute.
Keywords
three-component condensation, thermal and microwave activation, 4-Hydroxy-6-methyl-2H-pyran-2-one, aromatic aldehydes, urea, 3-[amino(aryl)-methyl]-4-hydroxy-6-methyl-2H-pyran-2-one, arylmethylenebis4-hydroxy-6-methyl-2H-pyran-2-one, 2-hydroxy-7-methyl-4-(3-nitrophenyl)-4,4a-dihydro-5H-pyrano[4,3-d]pyrimidine-5-one, NMR spectra
About the authors
I. V Kanevskaya
Saratov State University
Email: irinastrashilina@mail.ru
N. V Pchelintseva
Saratov State University
Email: irinastrashilina@mail.ru
O. V Fedotova
Saratov State University
Email: irinastrashilina@mail.ru
References
- McGlacken G.P., Fairlamb I.J.S. Nat. Prod. Rep. 2005, 22, 369-385. doi: 10.1039/B416651P
- Narasimhulu M., Krishna A.S., Rao J.V., Venkateswarlu Y. Tetrahedron. 2009, 65, 2989-2994. doi: 10.1016/j.tet.2009.01.101
- Shankar R., Chakravarti B., Singh U.S., Ansari M.I., Deshpande S., Dwivedi S.K., Bid H.K., Konwar R., Kharkwal G., Chandra V., Dwivedi A., Hajela K. Bioorg. Med. Chem. 2009, 17, 3847-3856. doi: 10.1016/j.bmc.2009.04.032
- Страшилина И.В., Мажукина О.А., Федотова О.В. ЖОрХ. 2018, 54, 103-106.
- Strashilina I.V., Mazhukina O.A., Fedotova O.V. Russ. J. Org. Chem. 2018, 54, 102-106. doi: 10.1134/S1070428018010098
- March P., Moreno-Mañas M., Casado J., Pleixats R., Roca J.L., Trius A. J. Heterocycl. Chem. 1984, 21, 85-89. doi: 10.1002/jhet.5570210119
- March P., Moreno-Mañas M., Pi R., Trius A. J. Heterocycl. Chem. 1982, 19, 335-336. doi: 10.1002/jhet.5570190223
- Zhang X., Qu Y., Fan X., Wang X., Wang J. J. Chem. Res. 2009, 8, 473-477. doi: 10.3184/030823409X465321
- Страшилина И.В., Арзямова Е.М., Федотова О.В. ЖОрХ. 2018, 54, 1162-1167.
- Strashilina I.V., Arziamova E.M., Fedotova O.V. Russ. J. Org. Chem. 2018, 54, 1173-1178. doi: 10.1134/S1070428018080092
- Pozharov M.V., Fedotova O.V., Kanevskaya I.V., Arzyamova E.M. Inorg. Chim. Acta. 2021, 517, 120207-120216. doi: 10.1016/j.ica.2020.120207
- Cervera M., Manas M., Pleixats R. Tetrahedron. 1990, 46, 7885-7892. doi: 10.1016/S0040-4020(01)90086-9
- Sweet F.S., Fissekis J.D. J. Am. Chem. Soc. 1973, 95, 8741-8749. doi: 10.1021/ja00807a040
- Kappe C.O. J. Org. Chem. 1997, 62, 7201-7204. doi: 10.1021/jo971010u
- Каневская И.В., Бондарцова А.С., Федотова О.В. ЖОрХ. 2020, 56, 1583-1589.
- Kanevskaya I.V., Bondartsova A.S., Fedotova O.V. Russ. J. Org. Chem. 2020, 56, 1753-1757. doi: 10.1134/S1070428020100139
